Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 11.9, Problem DQ
Interpretation Introduction
Interpretation:
The relative amount of trans-tetrol to cis-tetrol at
Concept Introduction:
Ring opening: Ring opening of epoxide takes place by acid-catalyzed hydrolysis of an epoxide.
Acid-catalyzed hydrolysis of an epoxide via
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7. Complete the following reactions by providing either necessary reagents or products.
CH₂ONa/H+
JUL
NaOH
Br
1). 0₂. 2). (CH₂)₂S
NaOH
CH₂₂/ZnCu
Bry/H₂O
Bry/CC
Draw the structure(s) of the major organic product(s) of the following reaction.
H,C.
1. NaOCH3 / CH3OH
2. 1 eq. 2-bromo-2-methylpropane
• You do not have to consider stereochemistry.
• Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)2 derived from N(i-Pr)2.
• If no reaction occurs, draw the organic starting material.
• If substantial starting material is present at the end of the reaction, include it in the products.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Separate structures with + signs from the drop-down menu.
1)
following reactions.
Give the major organic product or missing starting material for the
a)
1. add slowly
+ NaOCH2CH3
2. HCI
b)
1. NaOCH3, CH3OH
2. (CH3)2CHCH2CH2Br
3. H3O+, heat
ō
d)
2)
(NA).
1. NaOCH2CH3, CH3CH2OH
2. PhCH2CH2Br
3. H₂O+, heat
1. NaOCH 3, CH3OH
2. ?
HO
3. H3O+, heat
Classify each of the following as either aromatic (A) or nonaromatic
Chapter 11 Solutions
Organic Chemistry
Ch. 11.2 - Write IUPAC and common names for these ethers. (a)...Ch. 11.3 - Arrange these compounds in order of increasing...Ch. 11.4 - Show how you might use the Williamson ether...Ch. 11.4 - Show how ethyl hexyl ether might be prepared by a...Ch. 11.5 - Account for the fact that treatment of tert-butyl...Ch. 11.5 - Draw structural formulas for the major products of...Ch. 11.6 - Prob. 11.7PCh. 11.8 - Draw the expected products of Sharpless...Ch. 11.9 - Prob. AQCh. 11.9 - Prob. BQ
Ch. 11.9 - Prob. CQCh. 11.9 - Prob. DQCh. 11 - Write names for these compounds. Where possible,...Ch. 11 - Prob. 11.11PCh. 11 - Each compound given in this problem is a common...Ch. 11 - Account for the fact that tetrahydrofuran (THF) is...Ch. 11 - Prob. 11.14PCh. 11 - Write equations to show a combination of reactants...Ch. 11 - Propose a mechanism for this reaction.Ch. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Ethylene oxide is the starting material for the...Ch. 11 - Prob. 11.22PCh. 11 - Predict the structural formula of the major...Ch. 11 - The following equation shows the reaction of...Ch. 11 - Propose a mechanism to account for this...Ch. 11 - Acid-catalyzed hydrolysis of the following epoxide...Ch. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Propose a mechanism for the following...Ch. 11 - Show reagents and experimental conditions to...Ch. 11 - Starting with cis-3-hexene, show how to prepare...Ch. 11 - Show reagents to convert cycloheptene to each of...Ch. 11 - Show reagents to convert bromocyclopentane to each...Ch. 11 - Prob. 11.35PCh. 11 - Starting with acetylene and ethylene oxide as the...Ch. 11 - Following are the steps in the industrial...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Aldehydes and ketones react with one molecule of...Ch. 11 - Prob. 11.42PCh. 11 - Write the products of the following sequences of...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - During the synthesis of the antiasthmatic drug...Ch. 11 - Prob. 11.48P
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